103863-00-9Relevant academic research and scientific papers
Sulfonamide Synthesis via Calcium Triflimide Activation of Sulfonyl Fluorides
Mukherjee, Paramita,Woroch, Cristian P.,Cleary, Leah,Rusznak, Mark,Franzese, Ryan W.,Reese, Matthew R.,Tucker, Joseph W.,Humphrey, John M.,Etuk, Sarah M.,Kwan, Sabrina C.,Am Ende, Christopher W.,Ball, Nicholas D.
, p. 3943 - 3947 (2018)
A method using calcium triflimide [Ca(NTf2)2] as a Lewis acid to activate sulfonyl fluorides toward nucleophilic addition with amines is described. The reaction converts a wide array of sterically and electronically diverse sulfonyl fluorides and amines into the corresponding sulfonamides in good yield.
Metal Free Bi(hetero)aryl Synthesis: A Benzyne Truce-Smiles Rearrangement
Holden, Catherine M.,Sohel, Shariar M. A.,Greaney, Michael F.
supporting information, p. 2450 - 2453 (2016/02/18)
A new benzyne transformation is described that affords versatile biaryl structures without recourse to transition-metal catalysis or stoichiometric amounts of organometallic building blocks. Aryl sulfonamides add to benzyne upon fluoride activation, and then undergo an aryl Truce-Smiles rearrangement to afford biaryls with sulfur dioxide extrusion. The reaction proceeds under simple reaction conditions and has excellent scope for the synthesis of sterically hindered atropisomeric biaryl amines. All smiles: Metal-free biaryl synthesis is achieved by adding benzyne to arylsulfonamides. A Smiles rearrangement enables C-C bond formation, thus accessing a variety of functionalized biaryls under mild reaction conditions.
Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate
Colombe, James R.,Debergh, J. Robb,Buchwald, Stephen L.
, p. 3170 - 3173 (2015/06/30)
A method for the preparation of aryl and heteroaryl sulfonamides using 2,4,6-trichlorophenyl chlorosulfate (TCPC) is described. The reaction of 2-pyridylzinc reagents with TCPC resulted in 2,4,6-trichlorophenyl (TCP) pyridine-2-sulfonates, and the parent pyridine-2-sulfonate was shown to react with amines. Less electron-rich aryl- and heteroarylzinc reagents reacted with TCPC to afford sulfonyl chlorides that were converted in situ to sulfonamides.
Copper-catalyzed ortho-C-H amination of protected anilines with secondary amines
Martinez, Angel Manu,Rodriguez, Nuria,Arrayas, Ramon Gomez,Carretero, Juan C.
supporting information, p. 2801 - 2803 (2014/03/21)
A practical Cu-catalyzed picolinamide-directed o-amination of anilines showing excellent mono-substitution selectivity and high functional group tolerance has been developed.
Copper-catalyzed mild nitration of protected anilines
Hernando, Elier,Castillo, Rafael R.,Rodríguez, Nuria,G?mez Arrayás, Ram?n,Carretero, Juan C.
supporting information, p. 13854 - 13859 (2016/02/18)
A practical copper-catalyzed direct nitration of protected anilines, by using one equivalent of nitric acid as the nitrating agent, has been developed. This procedure features mild reaction conditions, wide structural scope (with regard to both N-protecting group and arene substitution), and high functional-group tolerance. Dinitration with two equivalents of nitric acid is also feasible. Practical and reliable: A Cu-catalyzed selective nitration of para- and ortho-substituted aniline derivatives by using one equivalent of HNO3 has been developed that produces water as the only stoichiometric byproduct (see scheme; PG=protecting group). This method is compatible with strongly electron-deficient substrates, enabling dinitration (by using 2.0 equiv of HNO3). This method allows for a rapid access to relevant nitrogen-containing heterocyclic architectures.
Copper-catalyzed ortho-halogenation of protected anilines
Urones, Beatriz,Martinez, Angel Manu,Rodriguez, Nuria,Arrayas, Ramon Gomez,Carretero, Juan C.
supporting information, p. 11044 - 11046 (2013/11/19)
A practical Cu-catalyzed direct ortho-halogenation of anilines under aerobic conditions has been developed. The reaction shows typically excellent mono-substitution selectivity, high ortho-regiocontrol and large functional group tolerance.
PdII-catalyzed C-H olefination of N-(2-pyridyl)sulfonyl anilines and arylalkylamines
Garcia-Rubia, Alfonso,Urones, Beatriz,Gomez Arrayas, Ramon,Carretero, Juan C.
, p. 10927 - 10931 (2012/01/04)
Flexible friend: The N-(2-pyridyl)sulfonyl group acts as a removable directing group in the PdII-catalyzed aryl C-H ortho alkenylation of N-alkyl aniline, benzylamine, and phenethylamine derivatives with electron-poor alkenes. The products were obtained in high yields (70-90 %) and with complete regiocontrol. The mild reductive N-sulfonyl removal enables the construction of a variety of nitrogen heterocycles. EWG=electron-withdrawing group.
Sulfonamidoquinoline/palladium(II)-dimer complex as a catalyst precursor for palladium-catalyzed γ-Selective and stereospecific allyl-aryl coupling reaction between allylic acetates and arylboronic acids
Makida, Yusuke,Ohmiya, Hirohisa,Sawamura, Masaya
supporting information; experimental part, p. 410 - 414 (2011/10/03)
On neutral territory: A neutral palladium(II)-dimer catalyst system incorporating anionic sulfonamidoquinoline ligands is effective for the γ-selective and stereospecific allyl-aryl coupling between acyclic (E)-allylic acetates and arylboronic acids. Copy
Deprotection of 2-pyridyl sulfonyl group from pyridine-2-sulfonamides by magnesium in methanol
Chwang Siek Pak,Dong Sung Lim
, p. 2209 - 2214 (2007/10/03)
Convenient deprotection of various pyridine-2-sulfonamides prepared by sulfonylation of primary and secondary amines with pyridine-2-sulfonylchloride was achieved by magnesium in methanol at 0°C to the corresponding amines in good yield.
Dication C(R1)-N(R2)2 synthons and their use in the synthesis of formamidines, amidines, and α-aminonitriles
Cai, Lisheng,Han, Ying,Ren, Sumei,Huang, Liangfu
, p. 8253 - 8262 (2007/10/03)
A combination of amides and 2-pyridinesulfonyl chloride was evaluated as synthons of the dication C(R1)-N(R2)2/2+. When the substrates were primary amines, high yields of formamidines and amidines were obtained. When the substrates were α-aminoamides, α-aminonitriles were obtained. Through this process, naturally occurring α-aminoacids can be transformed into chiral α-aminonitriles with complete retention of stereochemical configuration. All reactions proceed rapidly at room temperature, and normally finish within 10 min, with yields ranging from 80 to 95% for most cases. Among the sulfonyl chlorides examined, 2-pyridinesulfonyl chloride stands out in both reaction rate and selectivity of formamidine or amidine versus sulfonyl amide. The scope and limitations of the reaction among different types of amides as synthons and amines as substrates were examined. (C) 2000 Elsevier Science Ltd.
